Application of the tandem Stryker reduction-aldol cyclization strategy to the asymmetric synthesis of lucinone

被引:35
作者
Chiu, P [1 ]
Szeto, CP [1 ]
Geng, Z [1 ]
Cheng, KF [1 ]
机构
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
关键词
D O I
10.1016/S0040-4039(01)00638-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The tandem conjugate reduction-aldol cyclization using Stryker's reagent has been employed as the key-step in an asymmetric total synthesis of lucinone. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4091 / 4093
页数:3
相关论文
共 16 条
[1]   2 SESQUITERPENOIDS, LUCINONE AND GLUTINONE, FROM JASONIA-GLUTINOSA [J].
CASTILLO, LV ;
LANZA, AMD ;
FAURE, R ;
DEBRAUWER, L ;
ELIAS, R ;
BALANSARD, G .
PHYTOCHEMISTRY, 1995, 40 (04) :1193-1195
[2]   Total synthesis and stereochemistry of 13-hydroxy-α-eudesmol [J].
Chen, YG ;
Xiong, ZM ;
Zhou, G ;
Liu, LJ ;
Li, YL .
TETRAHEDRON-ASYMMETRY, 1998, 9 (11) :1923-1928
[3]   A conjugate reduction-intramolecular aldol strategy toward the synthesis of pseudolaric acid A [J].
Chiu, P ;
Chen, B ;
Cheng, KF .
TETRAHEDRON LETTERS, 1998, 39 (50) :9229-9232
[4]  
CHIU P, 2001, ORG LETT, V3
[5]  
GAO XP, 1987, J ORG CHEM, V52, P3192
[6]  
Ho T.-L., 1992, TANDEM ORGANIC REACT
[7]   CHEMISTRY OF CARBANIONS .24. COMPARISON OF STEREOCHEMISTRY IN ALKYLATION AND MICHAEL REACTION [J].
HOUSE, HO ;
UMEN, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (05) :1000-1003
[8]   A facile, general approach to the synthesis of electrophilic acetone equivalents [J].
Janicki, SZ ;
Fairgrieve, JM ;
Petillo, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3694-3700
[9]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[10]   SELECTIVE HYDRIDE-MEDIATED CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS USING [(PH3P)CUH]6 [J].
MAHONEY, WS ;
BRESTENSKY, DM ;
STRYKER, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (01) :291-293